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Synthesis 2008(18): 2977-2985  
DOI: 10.1055/s-2008-1067236
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

New α-Amido-α-aminonitrones As Building Blocks for Constructing ­Heterocyclic Systems

Bartosz Trzewik*, Dariusz Cież, Maciej Hodorowicz, Katarzyna Stadnicka
Faculty of Chemistry, Jagiellonian University, ul. Romana Ingardena 3, 30-060 Kraków, Poland
Fax: +48(12)6340515; e-Mail: trzewik@chemia.uj.edu.pl;
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Publikationsverlauf

Received 27 May 2008
Publikationsdatum:
22. August 2008 (online)

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Abstract

New, stable α-amido-α-aminonitrones were obtained in good yields from 3-oxobutyric acid N-pyridin-2-ylamides and nitrosobenzene. The α-amido-α-aminonitrones were then used as new, versatile building blocks to obtaining various heterocycles with both bielectrophilic and binucleophilic reagents. With diiodomethane as reagent, 1,2,5-oxadiazine derivatives were formed, whereas reactions with aromatic 1,2-, 1,3- and 1,4-diamines yielded quinoxaline, quinazoline, perimidine, and dibenzo[d,f][1,3]diazepine derivatives, respectively.

Key words

building blocks - nitrones - heterocycles - alkylation - cyclisation

    References

  • 1a Merino P. In Science of Synthesis   Vol. 27:  Padwa A. Thieme; Stuttgart: 2004.  p.511 
    Suche in Google Scholar
  • 1b Döpp D. Döpp H. In Houben-Weyl Methoden der Organische Chemie   Vol. E14b/2:  Klamann D. Hagemann H. Thieme; Stuttgart: 1990.  p.1533 
    Suche in Google Scholar
  • 1c Torsell KGB. In Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis   VCH Inc.; New York: 1988. 
  • 1d Cardona F. Goti A. Angew. Chem. Int. Ed.  2005,  44:  7832 
    Suche in Google Scholar
  • 1e Brandi A. Cicchi S. Cordero FM. Goti A. Chem. Rev.  2003,  103:  1213 
    Suche in Google Scholar
  • 1f Goti A. Cordero FM. Brandi A. Top. Curr. Chem.  1996,  178:  1 
    Suche in Google Scholar
  • 1g Pellissier H. Tetrahedron  2007,  63:  3235 
    Suche in Google Scholar
  • 1h Revuelta J. Cicchi S. Goti A. Brandi A. Synthesis  2007,  485 
  • 1i El Hassan I. Lauricella R. Tuccio B. Central Eur. J. Chem.  2006,  4:  338 
    Suche in Google Scholar
  • 1j Mottley C. Mason RP. In Biological Magnetic Resonance   Vol. 8:  Berliner LJ. Reuben J. Plenum Publishers; New York: 1989.  p.489 
    Suche in Google Scholar
  • 1k Tordo P. In Electron Paramagnetic Resonance   Vol. 16:  Gilbert BC. Atherton NM. Davies MJ. RSC Publishing; Cambridge: 1998.  p.116 
    Suche in Google Scholar
  • 1l Boruah M. Konwar D. Dutta D. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem.  2003,  42:  2112 
    Suche in Google Scholar
  • 1m Freisleben A. Schieberle P. Rychlik M. J. Agric. Food Chem.  2002,  50:  4760 
    Suche in Google Scholar
  • 1n Saito K. Kawamura A. Kanie T. Ueda Y. Kondo S. Heterocycles  2001,  55:  1071 
    Suche in Google Scholar
  • 2a Branco PS. Prabhakar S. Lobo AM. Williams DJ. Tetrahedron  1992,  48:  6335 
    Suche in Google Scholar
  • 2b Warshaw JA. Gallis DE. Acken BJ. Gonzalez OJ. Crist DR. J. Org. Chem.  1989,  54:  1736 
    Suche in Google Scholar
  • 2c Baiocchi L. Picconi G. Palacco G. J. Heterocycl. Chem.  1979,  16:  1477 
    Suche in Google Scholar
  • 2d Janzen EG. Nutter DE. Magn. Reson. Chem.  1997,  35:  131 
    Suche in Google Scholar
  • 2e Clement B. Kaempchen T. Arch. Pharm. (Weinheim, Ger.)  1987,  320:  566 
    Suche in Google Scholar
  • 2f Szantay C. Szabo L. Chem. Ber.  1965,  98:  1013 
    Suche in Google Scholar
  • 2g Aurich HG. Chem. Ber.  1968,  101:  1761 
    Suche in Google Scholar
  • 3a Hodorowicz M. Stadnicka K. Trzewik B. Zaleska B. Acta Crystallogr., Sect. E  2008,  64:  o599 
    Suche in Google Scholar
  • 3b Farrugia LJ. J. Appl. Crystallogr.  1997,  30:  565 
    Suche in Google Scholar
  • 3c Allen FH. Kennard O. Watson DG. Brammer L. Orpen AG. Taylor R. J. Chem. Soc., Perkin Trans. 2  1987,  1 
  • 3d Guimanini AG. Toniutti N. Verardo G. Merli M. Eur. J. Org. Chem.  1999,  1:  141 
    Suche in Google Scholar
  • 4a Zaleska B. Bazanek T. Socha R. Karelus M. Grochowski J. Serda P. J. Org. Chem.  2002,  67:  4526 
    Suche in Google Scholar
  • 4b Zaleska B. Socha R. Karelus M. Grochowski J. Serda P. Szneler E. J. Org. Chem.  2003,  68:  2334 
    Suche in Google Scholar
  • 4c Zaleska B. Trzewik B. Karelus M. Serda P. J. Chem. Res.  2007,  195 
  • 4d Zaleska B. Socha R. Monatsh. Chem.  2000,  131:  1061 
    Suche in Google Scholar
  • 5 Zaleska B. Socha R. Ciechanowicz-Rutkowska M. Pilati T. Monatsh. Chem.  2000,  131:  1151 
    CrossrefSuche in Google Scholar
  • 6 Zaleska B. Trzewik B. Stodolak E. Grochowski J. Serda P. Synthesis  2004,  2975 
    Thieme Connect
  • 7a Diels O. Leeden R. Chem. Ber.  1905,  38:  3363 
    Suche in Google Scholar
  • 7b Wright JB. J. Org. Chem.  1964,  29:  1620 
    Suche in Google Scholar
  • 8a Busch R. Kaemmerer H. Chem. Ber.  1930,  63:  653 
    Suche in Google Scholar
  • 8b Gnihtel H. Chem. Ber.  1970,  103:  3442 
    Suche in Google Scholar
  • 8c Gnihtel H. Chem. Ber.  1971,  104:  1512 
    Suche in Google Scholar
  • 8d Kiersznicki T. Rajca A. Pol. J. Chem.  1978,  52:  1827 
    Suche in Google Scholar
  • 8e Kamitori Y. Heterocycles  2000,  53:  107 
    Suche in Google Scholar
  • 8f Amitina SA. Grigor’ev IA. Tikhonov AYa. Russ. Chem. Bull.  2006,  55:  1046 
    Suche in Google Scholar
  • 8g Tselinskii IV. Mel’nikova SF. Pirogov SV. Russ. J. Org. Chem.  1997,  33:  1760 
    Suche in Google Scholar
  • 8h Gnichtel H. Moeller B. Chem. Ber.  1981,  114:  3170 
    Suche in Google Scholar
  • 8i Riddell FG. Turner ES. Tetrahedron  1979,  35:  1311 
    Suche in Google Scholar
  • 8j Coskun N. Sümengen D. Synth. Commun.  1993,  23:  1699 
    Suche in Google Scholar
  • 8k Marwaha A. Bharatamb PV. Mahajan MP. Tetrahedron Lett.  2005,  46:  8253 
    Suche in Google Scholar
  • 8l Marwaha A. Singh P. Mahajan MP. Tetrahedron  2006,  62:  5474 
    Suche in Google Scholar
  • 8m Gravestock MB. Knight DW. Malik KMA. Thornton SR. J. Chem. Soc., Perkin Trans. 1  2000,  3292 ; and references cited therein
  • 8n Gravestock MB. Knight DW. Thornton SR. J. Chem. Soc., Chem. Commun.  1993,  169 
  • 8o Gouverneur V. Ghosez L. Tetrahedron  1996,  52:  7585 ; and references cited therein
    Suche in Google Scholar
  • 8p Coskun N. Tat F. Gueven OO. Synth. Commun.  1999,  29:  3889 
    Suche in Google Scholar
  • 8q Billert T. Beckert R. Fehling P. Doring M. Brandenburg J. Gorls H. Langer P. J. Heterocycl. Chem.  1999,  36:  627 
    Suche in Google Scholar
  • 8r Nassar SA. Egypt. J. Chem.  2004,  47:  435 
    Suche in Google Scholar
  • 8s Madkour HMF. Heterocycl. Commun.  2002,  8:  501 
    Suche in Google Scholar
  • 8t Butter RN. McKenna EC. McMahon JM. Daly KM. Cunningham D. McArdle P. J. Chem. Soc., Perkin Trans. 1  1997,  2919 
  • 8u Butter RN. Daly KM. McMahon JM. Burke RA. J. Chem. Soc., Perkin Trans. 1  1997,  2919 
  • 8v Kliegel W. Frackenstein GH. Justus Liebigs Ann. Chem.  1977,  956 
  • 8w Ullmann EF. Coll L. Tseng SS. J. Am. Chem. Soc.  1973,  95:  1677 
    Suche in Google Scholar
  • 9a Agirbas H. Dueruest Y. Karahasanoglu A. Phosphorus, Sulfur Silicon Relat. Elem.  1996,  114:  173 
    Suche in Google Scholar
  • 9b Evenson GN. Moffett RB. J. Heterocycl. Chem.  1980,  351 
  • 9c Gnichtel H. Thiele S. Chem. Ber.  1971,  104:  1507 
    Suche in Google Scholar
  • 9d Geffken D. Zydowitz H. Ploetz A.
    Z. Naturforsch., B  2005,  60:  967 
    Suche in Google Scholar
  • 9e Zinner G. Schmidt J. Kilnig W. Arch. Pharm. (Weinheim, Ger.)  1980,  313:  35 
    Suche in Google Scholar
  • 9f Nakanishi S. Nantaku J. Otsuji Y. Chem. Lett.  1983,  341 
  • 9g Gouverneur V. Ghosez L. Tetrahedron  1996,  52:  7585 
    Suche in Google Scholar
  • For recent examples, see:
  • 10a Alonso F. Radivoy G. Yus M. Russ. Chem. Bull.  2003,  52:  2563 ; and references cited therein
    Suche in Google Scholar
  • 10b Alonso F. Radivoy G. Yus M. Synthesis  2001,  427 
  • 10c Chevrier C. LeNouen D. Neuburger M. Defoin A. Tarnus C. Tetrahedron Lett.  2004,  45:  5363 
    Suche in Google Scholar
  • 11a Ostrowska K. Kolasa A. In Science of Synthesis   Vol. 22:  Padwa A. Thieme; Stuttgart: 2004.  p.379 
    Suche in Google Scholar
  • 11b Langer P. Schroeder R. Eur. J. Org. Chem.  2004,  1025 
  • 11c Yoshimura J. Bull. Chem. Soc. Jpn.  1971,  44:  3131 
    Suche in Google Scholar
  • 11d Lozinskii MO. Shivanyuk AF. Pel"kis PS. Chem. Heterocycl. Compd. (Engl. Transl.)  1971,  7:  439 
    Suche in Google Scholar
  • 11e Ginsburg VA. Vasil’eva MN. J. Gen. Chem. USSR (Engl. Transl.)  1967,  37:  2371 
    Suche in Google Scholar
  • 11f Kroehnke F. Steuernagel HH. Chem. Ber.  1963,  96:  486 
    Suche in Google Scholar
  • 11g Lander GD. J. Chem. Soc.  1907,  91:  967 
    Suche in Google Scholar
  • 11h Lander GD. J. Chem. Soc.  1904,  85:  995 
    Suche in Google Scholar
  • 11i Lander GD. J. Chem. Soc.  1902,  81:  593 
    Suche in Google Scholar
  • 11j Anschuetz R. Stiepel J. Justus Liebigs Ann. Chem.  1899,  306:  14 
    Suche in Google Scholar
  • 11k Klinger H. Justus Liebigs Ann. Chem.  1877,  184:  280 
    Suche in Google Scholar
  • 11l Klinger H. Chem. Ber.  1875,  8:  312 
    Suche in Google Scholar
  • 12a Mason JC. Tennant G. J. Chem. Soc., Chem. Commun.  1972,  218 
  • 12b El-Sharief AMSh. Ammar YA. Mohamed YA. El-Gaby MSA. Phosphorus, Sulfur Silicon Relat. Elem.  1999,  148:  215 
    Suche in Google Scholar
  • 12c Ahmad Y. Habib MS. Iqbal M. Ziauddin . Bull. Chem. Soc. Jpn.  1965,  38:  562 
    Suche in Google Scholar
  • 12d Dudash J. Zhang Y. Moore JB. Look R. Liang Y. Beavers MP. Conway BR. Rybczynski PJ. Demarest KT. Bioorg. Med. Chem. Lett.  2005,  15:  4790 
    Suche in Google Scholar
  • 13a Sako S. Mem. Coll. Eng. Kyushu Imp. Univ.  1932,  6:  263 
    Suche in Google Scholar
  • 13b Insole JM. J. Chem. Soc. C  1971,  1712 
  • 13c Scherz MW. Fialeix M. Fischer JB. Laxma Reddy N. Server AC. Sonders MS. Tester BC. Weber E. Wong ST. Keana JFW. J. Med. Chem.  1990,  33:  2421 
    Suche in Google Scholar
  • 13d Ried W. Sinharay A. Chem. Ber.  1965,  98:  3523 
    Suche in Google Scholar
  • 13e Ried W. Sinharay A. Chem. Ber.  1964,  97:  1214 
    Suche in Google Scholar
  • 13f Fairfull AES. Peak DA. Short WF. Watkins TI. J. Chem. Soc.  1952,  4700 
  • 13g Matsuda K. Yanagisawa I. Isomura Y. Mase T. Shibanuma T. Synth. Commun.  1997,  27:  2393 
    Suche in Google Scholar
  • 13h Herr RJ. In Science of Synthesis   Vol. 17:  Weinreb SM. Thieme; Stuttgart: 2003. 
    Suche in Google Scholar
  • 14a de Aguiar A. Ber. Dtsch. Chem. Ges.  1874,  7:  309 
    Suche in Google Scholar
  • 14b Jung IG. Son SU. Park KH. Chung K.-Ch. Lee JW. Chung YK. Organometallics  2003,  22:  4715 
    Suche in Google Scholar
  • 14c Meric A. Incesu Z. Isikdag I. Farmaco  2002,  57:  543 
    Suche in Google Scholar
  • 14d Isikdag I. Meric A. Gyenes S. Incesu Z. Boll. Chim. Farm.  2004,  143:  110 ; Chem. Abstr. 2005, 142, 176767
    Suche in Google Scholar
  • 14e Maquestiau A. Berte L. Mayence A. Eynde J.-JV. Synth. Commun.  1991,  21:  2171 
    Suche in Google Scholar
  • 14f Yavari I. Adib M. Jahani-Moghaddam F. Bijanzadeh HR. Tetrahedron  2002,  58:  6901 
    Suche in Google Scholar
  • 14g Aly AA. El-Shaieb KM. Tetrahedron  2004,  60:  3797 
    Suche in Google Scholar
  • 14h Sachs F. Justus Liebigs Ann. Chem.  1909,  365:  162 
    Suche in Google Scholar
  • 14i King H. Wright EV. J. Chem. Soc.  1939,  253 
  • 14j Bazinet P. Yap GPA. Richeson DS. J. Am. Chem. Soc.  2003,  125:  13314 
    Suche in Google Scholar
  • 14k Maloshitskaya O. Sinkkonen J. Ovcharenko VV. Zelenin KN. Pihlaya K. Tetrahedron  2004,  60:  6913 
    Suche in Google Scholar
  • 14l Davis R. Tamaoki N. Org. Lett.  2005,  7:  1461 
    Suche in Google Scholar
  • 14m Borovlev I. V. Demidov O. P. Aksenov A. V. Pozharskii A. F. Russ. J. Org. Chem  2004,  40:  895 
    Suche in Google Scholar
  • 15a Maitraie D. Yakaiah T. Srinivas K. Reddy GV. Ravikanth S. Narsaiah B. Rao PS. Ravikumar K. Sridhar B. J. Fluorine Chem.  2006,  127:  351 
    Suche in Google Scholar
  • 15b Kidwai M. Saxena S. Khan MKR. Thukral SS. Eur. J. Med. Chem.  2005,  40:  816 
    Suche in Google Scholar
  • 15c Bathini Y. Sidhu I. Singh R. Micetish RG. Toogood PL. Tetrahedron Lett.  2002,  43:  3295 
    Suche in Google Scholar
  • 15d Seijas JA. Vázquez-Tato MP. Martínez MM. Tetrahedron Lett.  2000,  41:  2215 
    Suche in Google Scholar
  • 15e Preet M. Bedi S. Kumar V. Mahajan MP. Bioorg. Med. Chem. Lett.  2004,  14:  5211 
    Suche in Google Scholar
  • 15f Kumar V. Mohan C. Gupta M. Mahajan MP. Tetrahedron  2005,  61:  3533 
    Suche in Google Scholar
  • 16 Hodorowicz M. Stadnicka K. Trzewik B. Zaleska B. Acta Crystallogr., Sect. E  2007,  63:  o4115 
    CrossrefSuche in Google Scholar
  • 17a

    COLLECT, Nonius B. V.: Delft: The Netherlands, 2000

  • 17b Otwinowski Z. Minor W. In Methods in Enzymology   Vol. 276, Part A:  Carter CW. Sweet RM. Academic Press; New York: 1997.  p.307 
    Suche in Google Scholar
  • 17c Altomare A. Cascarano G. Giacovazzo C. Guagliardi A. Burla MC. Polidori G. Camalli M. J. Appl. Crystallogr.  1994,  27:  435 
    Suche in Google Scholar
  • 17d Sheldrick GM. Acta Crystallogr., Sect. A  1997,  64:  112 
    Suche in Google Scholar
  • 18 Fletcher DA. Gowenlock BG. Orrell KG. J. Chem. Soc., Perkin Trans. 2  1997,  2201 
    Crossref
  • 19 Shur M. Israelstam SS. J. Org. Chem.  1968,  33:  3015 
    CrossrefSuche in Google Scholar
20

Details of the X-ray crystal structure analysis for compounds 6a and 8a have been deposited in the Cambridge Crystallographic Data Centre, CCDC Nos. 683408 and 644908, respectively. Copies of this information may be obtained free of charge from The Director, CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(1223)336033;
e-mail: deposit@ccdc.cam.ac.uk].